Anna Wintour on Cardi B and Her Favorite Runway Show Ever

The new month brings with it a new Go Ask Anna, and just in time for couture, this one is keenly fashion-focused. What was AW’s first fashion job? What does she look for in an up-and-coming designer? Would she recommend attending design school? Can she single out her favorite fashion show of all time? Anna’s answers are suitably wide-ranging, whisking us from her girlhood in London, where she would help her father edit the Evening Standard’s fashion pages (then overseen by Suzy Menkes); to John Galliano’s iconic Fall 1994 collection, shown in São Schlumberger’s grand Parisian townhouse; and up to today, when she regularly urges young creatives to discover their own points of view—and not to skip school.

Anna also speaks to celebrity style, heaping special praise on the intrepid Cardi B, and considers the finer points of summer dressing. What’s a New Yorker to wear on an especially sticky day? A sleeveless dress, naturally. When did she first begin to wear her famous sunglasses? Long before you found your go-to pair, suffice it to say. And what, Emily Ratajkowski asks, is our editor’s favorite swimsuit? To this, Anna responds with a query of her own—speaking of points of view. “Emily,” she laughs, “why are you asking me that question?”